JP2005537291A - イミダゾ［１，２−ａ］ピリジン - Google Patents
イミダゾ［１，２−ａ］ピリジン Download PDFInfo
- Publication number
- JP2005537291A JP2005537291A JP2004525375A JP2004525375A JP2005537291A JP 2005537291 A JP2005537291 A JP 2005537291A JP 2004525375 A JP2004525375 A JP 2004525375A JP 2004525375 A JP2004525375 A JP 2004525375A JP 2005537291 A JP2005537291 A JP 2005537291A
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- JP
- Japan
- Prior art keywords
- pyridin
- methyl
- mmol
- alkyl
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 title 1
- 238000011282 treatment Methods 0.000 claims abstract description 13
- 239000003814 drug Substances 0.000 claims abstract description 9
- 230000001404 mediated effect Effects 0.000 claims abstract description 6
- 230000006806 disease prevention Effects 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 203
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 35
- -1 —CF 3 Chemical group 0.000 claims description 32
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 28
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 27
- 125000005843 halogen group Chemical group 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 125000001153 fluoro group Chemical group F* 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 229920006395 saturated elastomer Polymers 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 239000012453 solvate Substances 0.000 claims description 11
- CQTUYMRZAZVKDQ-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-3-[2-(4-methylsulfonylphenyl)pyridin-4-yl]imidazo[1,2-a]pyridine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2C=C(N=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)=N1 CQTUYMRZAZVKDQ-UHFFFAOYSA-N 0.000 claims description 10
- XGGCDVFQPLAMKA-UHFFFAOYSA-N 7-methyl-2-(6-methylpyridin-2-yl)-3-[2-[4-(2-pyrrolidin-1-ylethoxy)phenyl]pyridin-4-yl]imidazo[1,2-a]pyridine Chemical compound N1=C2C=C(C)C=CN2C(C=2C=C(N=CC=2)C=2C=CC(OCCN3CCCC3)=CC=2)=C1C1=CC=CC(C)=N1 XGGCDVFQPLAMKA-UHFFFAOYSA-N 0.000 claims description 10
- NBPMURLLBHYZII-UHFFFAOYSA-N 7-methyl-3-[2-[4-[(1-methylimidazol-4-yl)methoxy]phenyl]pyridin-4-yl]-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine Chemical compound N1=C2C=C(C)C=CN2C(C=2C=C(N=CC=2)C=2C=CC(OCC=3N=CN(C)C=3)=CC=2)=C1C1=CC=CC(C)=N1 NBPMURLLBHYZII-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- YSOAMSPADJLAHI-UHFFFAOYSA-N 2-[4-[4-[7-methyl-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyridin-2-yl]phenoxy]acetamide Chemical compound N1=C2C=C(C)C=CN2C(C=2C=C(N=CC=2)C=2C=CC(OCC(N)=O)=CC=2)=C1C1=CC=CC(C)=N1 YSOAMSPADJLAHI-UHFFFAOYSA-N 0.000 claims description 9
- 125000001246 bromo group Chemical group Br* 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- CCGRXCIJCYWWOY-UHFFFAOYSA-N 4-[4-[4-(2-pyridin-2-ylimidazo[1,2-a]pyridin-3-yl)pyridin-2-yl]phenyl]morpholine Chemical compound C1COCCN1C1=CC=C(C=2N=CC=C(C=2)C=2N3C=CC=CC3=NC=2C=2N=CC=CC=2)C=C1 CCGRXCIJCYWWOY-UHFFFAOYSA-N 0.000 claims description 8
- YSMRWZHDCKWGEE-UHFFFAOYSA-N [4-[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyridin-2-yl]phenyl]-morpholin-4-ylmethanone Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2C=C(N=CC=2)C=2C=CC(=CC=2)C(=O)N2CCOCC2)=N1 YSMRWZHDCKWGEE-UHFFFAOYSA-N 0.000 claims description 8
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- SFHCTSWZYNNONF-UHFFFAOYSA-N 2-pyridin-2-yl-3-[2-[4-(2-pyrrolidin-1-ylethoxy)phenyl]pyridin-4-yl]imidazo[1,2-a]pyridine Chemical compound C=1C=C(C=2N=CC=C(C=2)C=2N3C=CC=CC3=NC=2C=2N=CC=CC=2)C=CC=1OCCN1CCCC1 SFHCTSWZYNNONF-UHFFFAOYSA-N 0.000 claims description 3
- NPPIXSXSFGFFON-UHFFFAOYSA-N 3-[2-[4-(4-methylpiperazin-1-yl)phenyl]pyridin-4-yl]-2-pyridin-2-ylimidazo[1,2-a]pyridine Chemical compound C1CN(C)CCN1C1=CC=C(C=2N=CC=C(C=2)C=2N3C=CC=CC3=NC=2C=2N=CC=CC=2)C=C1 NPPIXSXSFGFFON-UHFFFAOYSA-N 0.000 claims description 3
- NQQMVZUQPDMLHG-UHFFFAOYSA-N 4-[[4-[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyridin-2-yl]phenyl]methyl]morpholine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2C=C(N=CC=2)C=2C=CC(CN3CCOCC3)=CC=2)=N1 NQQMVZUQPDMLHG-UHFFFAOYSA-N 0.000 claims description 3
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Classifications
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Cardiology (AREA)
- Neurology (AREA)
- Physical Education & Sports Medicine (AREA)
- Neurosurgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Addiction (AREA)
- Vascular Medicine (AREA)
- Oncology (AREA)
- Ophthalmology & Optometry (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Surgery (AREA)
- Pulmonology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0217783.0A GB0217783D0 (en) | 2002-07-31 | 2002-07-31 | Compounds |
| PCT/EP2003/008390 WO2004013138A2 (en) | 2002-07-31 | 2003-07-29 | Imidazo`1,2-a!pyridines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005537291A true JP2005537291A (ja) | 2005-12-08 |
| JP2005537291A5 JP2005537291A5 (enExample) | 2006-09-14 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004525375A Pending JP2005537291A (ja) | 2002-07-31 | 2003-07-29 | イミダゾ［１，２−ａ］ピリジン |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20050234029A1 (enExample) |
| EP (1) | EP1543003B1 (enExample) |
| JP (1) | JP2005537291A (enExample) |
| AR (1) | AR040724A1 (enExample) |
| AT (1) | ATE326467T1 (enExample) |
| AU (1) | AU2003255323A1 (enExample) |
| DE (1) | DE60305332T2 (enExample) |
| ES (1) | ES2259419T3 (enExample) |
| GB (1) | GB0217783D0 (enExample) |
| TW (1) | TW200413366A (enExample) |
| WO (1) | WO2004013138A2 (enExample) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005539000A (ja) * | 2002-07-31 | 2005-12-22 | スミスクライン・ビーチャム・コーポレイション | Ａｌｋ５阻害剤としての２−フェニルピリジン−４−イル誘導体 |
| JP2006502164A (ja) * | 2002-09-06 | 2006-01-19 | バイオジェン・アイデック・エムエイ・インコーポレイテッド | イミダゾロピリジンならびにその生成および使用方法 |
| JP2006519249A (ja) * | 2003-03-04 | 2006-08-24 | ファイザー・プロダクツ・インク | 形質転換成長因子（ｔｇｆ）阻害薬としての新規縮合複素芳香族化合物 |
| JP2011500623A (ja) * | 2007-10-17 | 2011-01-06 | ノバルティス アーゲー | ＡＬＫ阻害剤として有用なイミダゾ［１，２−ａ］ピリジン誘導体 |
| WO2011074658A1 (ja) * | 2009-12-18 | 2011-06-23 | 田辺三菱製薬株式会社 | 新規抗血小板薬 |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR039241A1 (es) | 2002-04-04 | 2005-02-16 | Biogen Inc | Heteroarilos trisustituidos y metodos para su produccion y uso de los mismos |
| MX2007011453A (es) | 2005-04-22 | 2008-02-12 | Alantos Pharmaceuticals Holding Inc | Inhibidores de la dipeptidil peptidasa-iv. |
| EP1928237A4 (en) * | 2005-09-02 | 2011-03-09 | Abbott Lab | NEW HETEROCYCLES BASED ON IMIDAZO |
| CN101611007A (zh) | 2006-12-20 | 2009-12-23 | 先灵公司 | 新颖的jnk抑制剂 |
| CA2672960A1 (en) * | 2006-12-20 | 2008-07-10 | Schering Corporation | Novel jnk inhibitors |
| WO2009086123A1 (en) * | 2007-12-21 | 2009-07-09 | Wyeth | Imidazo [1,2-a] pyridine compounds |
| EP2307402B1 (en) * | 2008-04-29 | 2012-11-07 | Novartis AG | Imidazo-pyridine derivatives as activin-like receptor kinase (alk4 or alk5) inhibitors |
| PH12012500778A1 (en) | 2009-10-30 | 2012-11-26 | Janssen Pharmaceutica Nv | IMIDAZO[1,2-b]PYRIDAZINE DERIVATIVES AND THEIR USE AS PDE10 INHIBITORS |
| AR080754A1 (es) | 2010-03-09 | 2012-05-09 | Janssen Pharmaceutica Nv | Derivados de imidazo (1,2-a) pirazina y su uso como inhibidores de pde10 |
| WO2011146287A1 (en) | 2010-05-20 | 2011-11-24 | Takeda Pharmaceutical Company Limited | Pyrazolo[4,3-b]pyridine-7-amine inhibitors of alk5 |
| US20120309796A1 (en) | 2011-06-06 | 2012-12-06 | Fariborz Firooznia | Benzocycloheptene acetic acids |
| JP6115962B2 (ja) | 2011-06-27 | 2017-04-19 | ヤンセン ファーマシューティカ エヌ．ベー． | １−アリール−４−メチル−［１，２，４］トリアゾロ［４，３−ａ］キノキサリン誘導体 |
| WO2014001314A1 (en) | 2012-06-26 | 2014-01-03 | Janssen Pharmaceutica Nv | Combinations comprising pde 2 inhibitors such as 1-aryl-4-methyl- [1,2,4] triazolo [4,3-a] quinoxaline compounds and pde 10 inhibitors for use in the treatment of neurological or metabolic disorders |
| AU2013289284B2 (en) | 2012-07-09 | 2017-03-30 | Janssen Pharmaceutica Nv | Inhibitors of phosphodiesterase 10 enzyme |
| CN108341769A (zh) * | 2018-05-13 | 2018-07-31 | 浙江凯普化工有限公司 | 多取代的6-氟皮考啉酸的制备方法 |
| CN115975224B (zh) * | 2023-03-16 | 2023-08-08 | 四川大学 | 一种pH/ROS双响应的组织粘附载药水凝胶及其制备方法和应用 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001072737A1 (en) * | 2000-03-27 | 2001-10-04 | Smithkline Beecham Corporation | Triarylimidazole derivatives as cytokine inhibitors |
| WO2002016359A1 (en) * | 2000-08-22 | 2002-02-28 | Glaxo Group Limited | Fused pyrazole derivatives being protein kinase inhibitors |
| WO2002040476A1 (en) * | 2000-11-16 | 2002-05-23 | Smithkline Beecham Corporation | Pyridyl-substituted triazoles as tgf inhibitors |
| WO2002040468A1 (en) * | 2000-11-16 | 2002-05-23 | Smithkline Beecham Corporation | Compounds |
| JP2005539000A (ja) * | 2002-07-31 | 2005-12-22 | スミスクライン・ビーチャム・コーポレイション | Ａｌｋ５阻害剤としての２−フェニルピリジン−４−イル誘導体 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11302177A (ja) * | 1998-04-27 | 1999-11-02 | Otsuka Pharmaceut Factory Inc | 腎炎治療剤 |
| GB0100762D0 (en) * | 2001-01-11 | 2001-02-21 | Smithkline Beecham Plc | Novel use |
-
2002
- 2002-07-31 GB GBGB0217783.0A patent/GB0217783D0/en not_active Ceased
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2003
- 2003-07-29 WO PCT/EP2003/008390 patent/WO2004013138A2/en not_active Ceased
- 2003-07-29 DE DE60305332T patent/DE60305332T2/de not_active Expired - Fee Related
- 2003-07-29 ES ES03766355T patent/ES2259419T3/es not_active Expired - Lifetime
- 2003-07-29 AU AU2003255323A patent/AU2003255323A1/en not_active Abandoned
- 2003-07-29 AT AT03766355T patent/ATE326467T1/de not_active IP Right Cessation
- 2003-07-29 EP EP03766355A patent/EP1543003B1/en not_active Expired - Lifetime
- 2003-07-29 TW TW092120589A patent/TW200413366A/zh unknown
- 2003-07-29 AR AR20030102720A patent/AR040724A1/es not_active Application Discontinuation
- 2003-07-29 US US10/522,967 patent/US20050234029A1/en not_active Abandoned
- 2003-07-29 JP JP2004525375A patent/JP2005537291A/ja active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001072737A1 (en) * | 2000-03-27 | 2001-10-04 | Smithkline Beecham Corporation | Triarylimidazole derivatives as cytokine inhibitors |
| WO2002016359A1 (en) * | 2000-08-22 | 2002-02-28 | Glaxo Group Limited | Fused pyrazole derivatives being protein kinase inhibitors |
| WO2002040476A1 (en) * | 2000-11-16 | 2002-05-23 | Smithkline Beecham Corporation | Pyridyl-substituted triazoles as tgf inhibitors |
| WO2002040468A1 (en) * | 2000-11-16 | 2002-05-23 | Smithkline Beecham Corporation | Compounds |
| JP2005539000A (ja) * | 2002-07-31 | 2005-12-22 | スミスクライン・ビーチャム・コーポレイション | Ａｌｋ５阻害剤としての２−フェニルピリジン−４−イル誘導体 |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005539000A (ja) * | 2002-07-31 | 2005-12-22 | スミスクライン・ビーチャム・コーポレイション | Ａｌｋ５阻害剤としての２−フェニルピリジン−４−イル誘導体 |
| JP2006502164A (ja) * | 2002-09-06 | 2006-01-19 | バイオジェン・アイデック・エムエイ・インコーポレイテッド | イミダゾロピリジンならびにその生成および使用方法 |
| JP2006519249A (ja) * | 2003-03-04 | 2006-08-24 | ファイザー・プロダクツ・インク | 形質転換成長因子（ｔｇｆ）阻害薬としての新規縮合複素芳香族化合物 |
| JP2011500623A (ja) * | 2007-10-17 | 2011-01-06 | ノバルティス アーゲー | ＡＬＫ阻害剤として有用なイミダゾ［１，２−ａ］ピリジン誘導体 |
| WO2011074658A1 (ja) * | 2009-12-18 | 2011-06-23 | 田辺三菱製薬株式会社 | 新規抗血小板薬 |
| JPWO2011074658A1 (ja) * | 2009-12-18 | 2013-05-02 | 田辺三菱製薬株式会社 | 新規抗血小板薬 |
| US8703760B2 (en) | 2009-12-18 | 2014-04-22 | Mitsubishi Tanabe Pharma Corporation | Antiplatelet agent |
| AU2010331175B2 (en) * | 2009-12-18 | 2014-08-28 | Mitsubishi Tanabe Pharma Corporation | Novel antiplatelet agent |
| US9533983B2 (en) | 2009-12-18 | 2017-01-03 | Mitsubishi Tanabe Pharma Corporation | Antiplatelet agent |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003255323A1 (en) | 2004-02-23 |
| AU2003255323A8 (en) | 2004-02-23 |
| GB0217783D0 (en) | 2002-09-11 |
| AR040724A1 (es) | 2005-04-20 |
| ES2259419T3 (es) | 2006-10-01 |
| TW200413366A (en) | 2004-08-01 |
| EP1543003B1 (en) | 2006-05-17 |
| DE60305332D1 (de) | 2006-06-22 |
| WO2004013138A3 (en) | 2004-03-25 |
| US20050234029A1 (en) | 2005-10-20 |
| DE60305332T2 (de) | 2007-04-19 |
| EP1543003A2 (en) | 2005-06-22 |
| ATE326467T1 (de) | 2006-06-15 |
| WO2004013138A2 (en) | 2004-02-12 |
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